Not Always the First Saturday in May: The Kentucky Derby’s Changing Calendar

For modern racing fans, the first Saturday in May means that it is time once again to break out the big hats and mint julep glasses while singing “My Old Kentucky Home” and celebrating another year of the Kentucky Derby. Yet the 150-year history of this quintessential American sporting event has seen a few changes to its calendar. Through war, pandemic, and the ever-evolving sport of horse racing, the Run for the Roses has rolled with the punches, finally settling into its familiar place on our calendar.

From the Start  

When Colonel Meriwether Lewis Clark returned from his travels abroad, the young entrepreneur was ready to create a showplace for Kentucky racing with the Kentucky Derby, modeled on its famed cousin, the Epsom Derby, as its centerpiece. He filed letters of incorporation for the Louisville Jockey Club and Driving Park Association in June 1874 with the goal of holding that first race the following spring. The schedule was ambitious, but work commenced with haste, with the grandstand and clubhouse completed that fall, and the first horses shipped in the following April. On May 17, 1875, a Monday, Louisville’s newest racetrack, which would be christened Churchill Downs in 1883, celebrated the opening day of its inaugural meet, highlighted by the first Kentucky Derby, won by Henry Price McGrath’s Aristides. 

For the next forty-seven years, the Derby remained in the same place, staged on the first day of Churchill Downs’ spring meet, first under the management of its founder Colonel Clark and then later under Colonel Matt Winn. Winn made the race his business when he and a syndicate of local horsemen bought the flailing racetrack in 1902; the former tailor then became general manager and set about remaking the Kentucky Derby as the prestigious three-year-old stakes he imagined it to be. 

While Winn introduced newer concepts like pari-mutuel wagering and the $2 bet during his tenure, he did not change the date of the big race. Though the day of the week was not consistent — the only day of the week the race was not contested was Sunday — its position as the feature on the first day of the meet remained the same until the rising status of another important stakes race meant that the Derby faced a dilemma. 

A Necessary Change

Survivor won the first Preakness Stakes at Pimlico Race Course in Baltimore, Maryland, a full two years before Aristides won the inaugural Kentucky Derby. By 1890, financial issues put an end to racing at Pimlico; the Preakness then moved to New York, where a stakes race of the same name appeared on the stakes schedule first for Morris Park and then later for Gravesend Race Track. When the race returned to Pimlico in 1909, the Maryland Jockey Club made it the feature of the last day of each spring meet, but its smaller purse was not enough to help the stakes compete with its brawnier Kentucky cousin. 

On May 12, 1917, at 4:46 p.m., 14 horses faced the barrier at Pimlico, with Kalitan winning the $5,000 purse for Colonel E.R. Bradley. Seven minutes later and hundreds of miles away, Omar Khayyam beat a field of 14 others to become the first English-bred horse to win the Kentucky Derby, pocketing a purse of $16,600. The overlap was not consequential enough to merit a mention in the Daily Racing Form or elsewhere. At this point in racing history, only three horses had ever run in both races: Vagabond in 1875; Hindus, who would win that year’s Preakness at Gravesend in 1900; and Norse King in 1915. By the time the two were scheduled for the same day in 1922, just five years later, everything had changed. 

In 1918, the Maryland Jockey Club, headed by William P. Riggs, decided to bump the Preakness’ purse to $15,000, the same money that the Derby would award its winner that year. That additional number lured enough starters for the Preakness that the race was split into two divisions, the only time that has happened in the race’s history. Each division came with the same $15,000 purse, luring Derby fourth-place War Cloud to Baltimore. After winning one of the two divisions, War Cloud finished second in the Belmont. The money he collected over those three races was enough to make owners and trainers take notice. 

When Sir Barton won all three races the following year, he collected $63,350 for his efforts, a substantial amount of money. In 1920 and then 1921, the Derby-Preakness double became an attractive goal for any trainers and owners with a good three-year-old, though no one would duplicate Sir Barton’s double for some time yet. The scheduling remained the same even with the increased purses; the Derby was the first day of Churchill’s spring meet and the Preakness was on the last day of Pimlico’s. In 1922, those happened to be the same day, May 13. 

When the schedules came out in early 1922, horsemen called for each racetrack to reconsider their calendars. Instead, Riggs and Winn responded by bumping up their race’s purse in an effort to lure potential starters, especially the favored Morvich, to their racetrack. Neither wanted to back down and change the date, much to the chagrin of trainers and owners of the year’s good three-year-olds. By the time all was said and done, the purse for each race was a cool $50,000, but neither relented on the schedule. Pillory would win the $50,000 Preakness at Pimlico while almost 600 miles away and 10 minutes later, Morvich would take the $50,000 Kentucky Derby.

In the aftermath of this overlap, the two racetracks agreed on a change. The Preakness would be first, and then a week or so later would come the Kentucky Derby, a schedule that enabled horses to run in both. The goal was to give more horses the opportunity to win the nascent Triple Crown, which was growing in popularity throughout the 1920s. 

Rolling with the Times  

The problem was, even with the change in schedule, the dates of the two races still varied from year to year. In 1924, the two were five days apart. Between 1924 and 1931, the time between the two was anywhere from five to eight days. Add in the logistics of travel between the two racetracks, and the time between was proving problematic for those trying to win both. With that in mind, Colonel Winn and Churchill Downs moved the Derby to the first Saturday in May, with the Preakness setting into its new slot a week later. By 1950, the gap was two weeks between the races. 

The Derby’s current spot as the first Saturday in May has been in place for nearly a century with two exceptions. Wartime restrictions meant that the 1945 Kentucky Derby was delayed until June 9, with the Preakness a week later. In 2020, Churchill Downs moved the Derby from its permanent home on the first Saturday in May to the first Saturday in September as the COVID-19 pandemic required a number of sports to adapt their schedules. Since 2021, the Run for the Roses has returned to its famed spot on our racing calendar. 

The Kentucky Derby's schedule has evolved significantly since its inaugural race in 1875, reflecting the broader changes in the sport of horse racing and American culture. The move to its iconic home on the first Saturday in May has helped solidify its identity as the Run for the Roses and the first leg of the prestigious Triple Crown. This evolving schedule highlights the race’s enduring appeal and adaptability, ensuring that this singular sporting experience remains a cherished tradition in American sports.